# US 9,040,741 B2 · Catalytic dehydration of alcohols using non-volatile acid catalysts

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- Number: US 9,040,741 B2
- Document ID: US9040741B2
- Status: Granted
- Kind: B2
- Application number: 13/497,627
- Filed: 2010-07-29
- Published: 2012-08-30
- Granted: 2015-05-26
- Earliest claimed: 2009-09-24
- Assignees: Signa Chemistry, Inc.
- Applicants: Michael Lefenfeld; Robert Hoch
- Inventors: Michael Lefenfeld; Robert Hoch
- Web page: https://patentgrep.com/patent/US9040741B2

## CPC

- C07C 1/24: by elimination of water
- C07C 2529/40: of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11
- C07C 2529/83: Aluminophosphates (APO compounds)
- C07C 2529/84: Aluminophosphates containing other elements, e.g. metals, boron
- C07C 2529/85: Silicoaluminophosphates (SAPO compounds)
- Y02P 20/10: Process efficiency
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

A catalytic process for dehydration of an aliphatic C2-C6 alcohol to its corresponding olefin is disclosed. The process continuously flows through a reaction zone a liquid phase containing an aliphatic C2-C6 alcohol to contact a non-volatile acid catalyst at a reaction temperature and pressure to at least partially convert the aliphatic C2-C6 alcohol in the liquid phase to its corresponding olefin. The reaction pressure is greater than atmospheric pressure and the reaction temperature is above the boiling point of the olefin at reaction pressure, but below the critical temperature of the alcohol, and the olefin product is substantially in the gaseous phase. After the contacting step, the olefin containing gaseous phase is separated from the liquid phase. The invention also relates to catalytic processes such as a hydrolysis of an olefin to an alcohol, an esterification, a transesterification, a polymerization, an aldol condensation or an ester hydrolysis.

## Claims

### Claim 1

A catalytic process for dehydration of an aliphatic C2-C6 alcohol to its corresponding olefin comprising the steps of:
continuously flowing through a reaction zone a liquid phase containing an aliphatic C2-C6 alcohol to contact a non-volatile acid catalyst at a reaction temperature and pressure to at least partially convert the aliphatic C2-C6 alcohol in the liquid phase to its corresponding olefin and water, wherein the reaction pressure is greater than atmospheric pressure and the reaction temperature is above the boiling point of the olefin at reaction pressure, but below the critical temperature of the alcohol, and the olefin product is substantially in the gaseous phase; and
separating said olefin containing gaseous phase from the liquid phase;
wherein the water is recovered by distillation.

### Claim 2 (depends on 1)

The catalytic process of claim 1, further comprising the steps of:
recovering at least a portion of the liquid phase as a reaction effluent;
optionally recovering any unconverted aliphatic C2-C6 alcohol from the olefin-containing gaseous phase or from the reaction effluent; and
optionally recycling any unconverted alcohol to the reaction zone.

### Claim 3 (depends on 1)

A catalytic process of claim 1 wherein the reaction conditions comprise a reaction pressure which is greater than 10 atm.

### Claim 4 (depends on 1)

A catalytic process of claim 1 wherein the reaction conditions comprise a reaction pressure which is greater than 20 atm.

### Claim 5 (depends on 1)

A catalytic process of claim 1 wherein the reaction conditions comprise a reaction pressure which is greater than 30 atm.

### Claim 6 (depends on 1)

A catalytic process of claim 1 wherein the separating step comprises removing gas phase olefin product from liquid phase alcohol in the reaction zone.

### Claim 7 (depends on 1)

A catalytic process of claim 1 where the reaction zone is a trickle bed reaction zone.

### Claim 8 (depends on 7)

A catalytic process of claim 7 where the Weight Hourly Space Velocity (WHSV) is between 0.1 and 10.

### Claim 9 (depends on 7)

A catalytic process of claim 7 where the reaction zone has a gas/liquid ratio of between 0.1 and 5.

### Claim 10 (depends on 1)

A catalytic process of claim 1 where the reaction zone is a boiling reactor zone.

### Claim 11 (depends on 1)

A catalytic process of claim 1 comprising the steps of:
recovering at least a portion of the liquid phase as a reaction effluent;
recovering any uncoverted aliphatic C2-C6 alcohol from the olefin-containing gaseous phase or from the reaction effluent; and
recycling any unconverted alcohol to the reaction zone.

### Claim 12 (depends on 1, 11)

A catalytic process of claim 1 or 11 wherein the liquid phase has water content in excess of the water/alcohol azeotrope.

### Claim 13 (depends on 1, 11)

A process of claim 1 or 11 where the alcohol is ethanol.

### Claim 14 (depends on 1)

The catalytic process of claim 1, wherein the non-volatile acid catalyst is a solid acid catalyst.

### Claim 15 (depends on 14)

The catalytic process of claim 14, wherein the non-volatile acid catalyst is an AIPO catalyst.